(Z)-2-methyl-4-phenyl-3-butenenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-methyl-4-phenyl-3-butenenitrile
• 英文别名: (Z)-2-methyl-4-phenylbut-3-enenitrile
• 化学式: C₁₁H₁₁N
• 分子量: 157.215
• InChiKey: QFYUIQMDJGQTGR-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯丙腈 、 β-溴苯乙烯 在 (2,2'-bipyridine)nickel(II) dibromide tetrabutylammonium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-2-methyl-4-phenylbut-3-enenitrile 、 (Z)-2-methyl-4-phenyl-3-butenenitrile
  参考文献：
  名称：

  Nickel-Catalyzed Electrochemical Couplings of Vinyl Halides:  Synthetic and Stereochemical Aspects

  摘要：

  Homo- and cross-coupling involving alkenyl halides have been performed efficiently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, beta,gamma- or gamma,delta-unsaturated esters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepared with high yields and high stereoselectivity. Partial isomerization is only observed in a few cases, when the alkenyl halide is involved in a late step of the catalytic cycle. This is the case in the preparation of (Z,Z)-1,3-diene.

  DOI：

  10.1021/jo000182f

文献信息

• Nickel-Catalyzed Electrochemical Couplings of Vinyl Halides:  Synthetic and Stereochemical Aspects
  作者：C. Cannes、S. Condon、M. Durandetti、J. Périchon、J.-Y. Nédélec

  DOI：10.1021/jo000182f

  日期：2000.7.1

  Homo- and cross-coupling involving alkenyl halides have been performed efficiently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, beta,gamma- or gamma,delta-unsaturated esters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepared with high yields and high stereoselectivity. Partial isomerization is only observed in a few cases, when the alkenyl halide is involved in a late step of the catalytic cycle. This is the case in the preparation of (Z,Z)-1,3-diene.